Winter Park, FL Investment Properties for Sale
Browse homes for sale and investment properties in Winter Park, FL. Refine your search by price, property type, or more.
Best cash flowing properties in Winter Park, FL
Active
$139,900
2
bds
|
3
ba
|
1,085
sqft
|
built
1974
7449 Daniel Webster Dr, Winter Park, FL 32792
$301
Cash flow
11.2%
Cash-on-Cash Return
8.7%
Cap rate
1.2%
Rent to Value Ratio
Active
$225,000
2
bds
|
1
ba
|
808
sqft
|
built
1984
851 Miles Ave, Winter Park, FL 32789
$7
Cash flow
0.2%
Cash-on-Cash Return
6.2%
Cap rate
0.8%
Rent to Value Ratio
251 out of 289 properties for sale in Winter Park, FL
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Pending
$575,000
4
bds
|
3
ba
|
2,219
sqft
|
built
1972
7852 Broken Arrow Trl, Winter Park, FL 32792
$-1,309
Cash flow
-11.9%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Pending
$429,000
3
bds
|
2
ba
|
1,140
sqft
|
built
1961
2809 Sanbina St, Winter Park, FL 32789
$-990
Cash flow
-12.0%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$3,599,999
5
bds
|
6
ba
|
4,955
sqft
|
built
2017
1761 Legion Dr, Winter Park, FL 32789
$-16,284
Cash flow
-23.6%
Cash-on-Cash Return
0.7%
Cap rate
0.2%
Rent to Value Ratio
Active
$525,000
4
bds
|
3
ba
|
2,075
sqft
|
built
1987
1976 Shadyhill Ter, Winter Park, FL 32792
$-515
Cash flow
-5.1%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$489,000
3
bds
|
2
ba
|
1,623
sqft
|
built
1959
2648 Amsden Rd, Winter Park, FL 32792
$-957
Cash flow
-10.2%
Cash-on-Cash Return
3.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$299,900
3
bds
|
1
ba
|
1,114
sqft
|
built
1956
7102 Easter St, Winter Park, FL 32792
$-114
Cash flow
-2.0%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$575,000
3
bds
|
2
ba
|
1,867
sqft
|
built
1979
1387 Sawgrass Ct, Winter Park, FL 32792
$-1,227
Cash flow
-11.1%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,500,000
4
bds
|
4
ba
|
3,349
sqft
|
built
2014
2401 Lafayette Ave, Winter Park, FL 32789
$-4,952
Cash flow
-17.2%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,210,000
4
bds
|
4
ba
|
3,321
sqft
|
built
1992
4048 Gilder Rose Pl, Winter Park, FL 32792
$-4,127
Cash flow
-17.8%
Cash-on-Cash Return
2.1%
Cap rate
0.3%
Rent to Value Ratio
Active
$635,000
2
bds
|
1
ba
|
789
sqft
|
built
1953
1339 Orchid Ave, Winter Park, FL 32789
$-1,965
Cash flow
-16.1%
Cash-on-Cash Return
2.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$195,000
2
bds
|
2
ba
|
1,049
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-299
Cash flow
-8.0%
Cash-on-Cash Return
4.3%
Cap rate
0.8%
Rent to Value Ratio
Pending
$949,900
3
bds
|
3
ba
|
1,981
sqft
|
built
1960
609 Langholm Dr, Winter Park, FL 32789
$-2,916
Cash flow
-16.0%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,425,000
4
bds
|
4
ba
|
3,153
sqft
|
built
2019
2922 Reef Knot Pl, Winter Park, FL 32792
$-4,568
Cash flow
-16.7%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$775,000
3
bds
|
2
ba
|
1,598
sqft
|
built
1958
1961 Winter Park Rd, Winter Park, FL 32789
$-2,753
Cash flow
-18.5%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$127,000
2
bds
|
2
ba
|
1,066
sqft
|
built
1974
3057 Aaron Burr Ave, Winter Park, FL 32792
$-122
Cash flow
-5.0%
Cash-on-Cash Return
5.0%
Cap rate
1.3%
Rent to Value Ratio
Active
$474,900
3
bds
|
3
ba
|
2,308
sqft
|
built
2019
1624 Little Wren Ln, Winter Park, FL 32792
$-1,219
Cash flow
-13.4%
Cash-on-Cash Return
3.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$650,000
2
bds
|
2
ba
|
1,311
sqft
|
built
1982
300 Carolina Ave, Winter Park, FL 32789
$-2,181
Cash flow
-17.5%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$225,000
2
bds
|
1
ba
|
808
sqft
|
built
1984
851 Miles Ave, Winter Park, FL 32789
$7
Cash flow
0.2%
Cash-on-Cash Return
6.2%
Cap rate
0.8%
Rent to Value Ratio
Active
$465,000
4
bds
|
0
ba
|
2,000
sqft
|
built
1980
131 Stefanik Rd, Winter Park, FL 32792
$-1,379
Cash flow
-15.5%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
Pending
$567,000
3
bds
|
2
ba
|
1,420
sqft
|
built
1957
1901 Loch Berry Rd, Winter Park, FL 32792
$-1,571
Cash flow
-14.5%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,399,000
3
bds
|
4
ba
|
3,440
sqft
|
built
2001
922 N Pennsylvania Ave, Winter Park, FL 32789
$-9,702
Cash flow
-21.1%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$465,000
4
bds
|
0
ba
|
2,000
sqft
|
built
1981
2608 Dora Ct, Winter Park, FL 32792
$-1,312
Cash flow
-14.7%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$379,500
3
bds
|
2
ba
|
1,637
sqft
|
built
1983
1050 Reading Ct, Winter Park, FL 32792
$-637
Cash flow
-8.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$610,000
3
bds
|
2
ba
|
1,875
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-1,686
Cash flow
-14.4%
Cash-on-Cash Return
2.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$355,000
3
bds
|
3
ba
|
1,406
sqft
|
built
2020
3118 Crown Jewel Ct, Winter Park, FL 32792
$-715
Cash flow
-10.5%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Pending
$290,000
2
bds
|
2
ba
|
1,020
sqft
|
built
1977
2541 Leeward Way, Winter Park, FL 32792
$-823
Cash flow
-14.8%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$420,000
3
bds
|
2
ba
|
1,613
sqft
|
built
2003
5559 Pats Pt, Winter Park, FL 32792
$-1,050
Cash flow
-13.0%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,300,000
5
bds
|
6
ba
|
4,263
sqft
|
built
2015
1820 Englewood Rd, Winter Park, FL 32789
$-12,116
Cash flow
-19.2%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$305,000
3
bds
|
2
ba
|
1,284
sqft
|
built
1979
2376 Dominica Run, Winter Park, FL 32792
$-489
Cash flow
-8.4%
Cash-on-Cash Return
4.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$425,000
3
bds
|
2
ba
|
1,675
sqft
|
built
1981
2003 Bentwood Dr, Winter Park, FL 32792
$-354
Cash flow
-4.3%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$192,000
2
bds
|
2
ba
|
840
sqft
|
built
1990
3651 N Goldenrod Rd, Winter Park, FL 32792
$-48
Cash flow
-1.3%
Cash-on-Cash Return
5.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$650,000
4
bds
|
2
ba
|
2,003
sqft
|
built
1981
1507 Golfside Dr, Winter Park, FL 32792
$-1,343
Cash flow
-10.8%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$139,900
2
bds
|
3
ba
|
1,085
sqft
|
built
1974
7449 Daniel Webster Dr, Winter Park, FL 32792
$301
Cash flow
11.2%
Cash-on-Cash Return
8.7%
Cap rate
1.2%
Rent to Value Ratio
Pending
$740,000
3
bds
|
2
ba
|
2,245
sqft
|
built
1957
1840 Laurel Rd, Winter Park, FL 32789
$-2,358
Cash flow
-16.6%
Cash-on-Cash Return
2.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,180,000
4
bds
|
4
ba
|
2,770
sqft
|
built
2018
2607 Lafayette Ave, Winter Park, FL 32789
$-4,094
Cash flow
-18.1%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$570,000
4
bds
|
2
ba
|
1,749
sqft
|
built
1965
3231 Lowndes Dr, Winter Park, FL 32792
$-1,470
Cash flow
-13.5%
Cash-on-Cash Return
3.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$365,900
3
bds
|
3
ba
|
1,628
sqft
|
built
2003
2548 Galliano Cir, Winter Park, FL 32792
$-694
Cash flow
-9.9%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Pending
$269,000
1
bds
|
1
ba
|
736
sqft
|
built
1948
1979 Staunton Ave, Winter Park, FL 32789
$-281
Cash flow
-5.5%
Cash-on-Cash Return
4.9%
Cap rate
0.6%
Rent to Value Ratio
Pending
$779,000
5
bds
|
3
ba
|
3,493
sqft
|
built
1969
103 Longhorn Rd, Winter Park, FL 32792
$-1,743
Cash flow
-11.7%
Cash-on-Cash Return
3.5%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,125,000
5
bds
|
5
ba
|
3,839
sqft
|
built
1993
2880 Old Castle Dr, Winter Park, FL 32792
$-3,590
Cash flow
-16.6%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio